TY - JOUR
T1 - Hanultarin, a cytotoxic lignan as an inhibitor of actin cytoskeleton polymerization from the seeds of Trichosanthes kirilowii
AU - Moon, Surk Sik
AU - Rahman, Aziz Abdur
AU - Kim, Joo Young
AU - Kee, Sun Ho
N1 - Funding Information:
This work was supported by grants from the Korea Science and Engineering Foundation (Grant No. KOSEF R01-2003-000-10458-0) and in part by the Korean Research Foundation Grant funded by the Korean Government (MOEHRD, 2004) for A. A. Rahman.
PY - 2008/8/1
Y1 - 2008/8/1
N2 - Bioactivity-directed fractionation of extracts from the seeds of Trichosanthes kirilowii led to the isolation of (-)-1-O-feruloylsecoisolariciresinol (2), named hanultarin, In addition, four known lignans were also isolated, including (-)-secoisolariciresinol (1), 1,4-O-diferuloylsecoisolariciresinol (3), (-)-pinoresinol (4), and 4-ketopinoresinol (5). Their structures were elucidated on the basis of spectroscopic data. Compounds 2 and 3 exhibited strong cytotoxic effects against human lung carcinoma A549 cells, melanoma SK-Mel-2 cells, and mouse skin melanoma B16F1 cells with IC50 ranges of 3-13 μg/mL. Compound 2 showed an inhibitory effect on the polymerization of the actin cytoskeleton in normal epidermal keratinocyte (HaCaT cells), suggesting unique biological properties of compound 2 compared to those of the other isolates.
AB - Bioactivity-directed fractionation of extracts from the seeds of Trichosanthes kirilowii led to the isolation of (-)-1-O-feruloylsecoisolariciresinol (2), named hanultarin, In addition, four known lignans were also isolated, including (-)-secoisolariciresinol (1), 1,4-O-diferuloylsecoisolariciresinol (3), (-)-pinoresinol (4), and 4-ketopinoresinol (5). Their structures were elucidated on the basis of spectroscopic data. Compounds 2 and 3 exhibited strong cytotoxic effects against human lung carcinoma A549 cells, melanoma SK-Mel-2 cells, and mouse skin melanoma B16F1 cells with IC50 ranges of 3-13 μg/mL. Compound 2 showed an inhibitory effect on the polymerization of the actin cytoskeleton in normal epidermal keratinocyte (HaCaT cells), suggesting unique biological properties of compound 2 compared to those of the other isolates.
KW - Actin cytoskeleton
KW - Actin polymerization
KW - Hanultarin
KW - Secoisolariciresinol
KW - Trichosanthes kirilowii
UR - http://www.scopus.com/inward/record.url?scp=48449088236&partnerID=8YFLogxK
U2 - 10.1016/j.bmc.2008.06.032
DO - 10.1016/j.bmc.2008.06.032
M3 - Article
C2 - 18603435
AN - SCOPUS:48449088236
SN - 0968-0896
VL - 16
SP - 7264
EP - 7269
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
IS - 15
ER -